Final Resting
Quest Information
Starting Location: Crucible
Starting NPC: Hirrus Clutumnus
Possible Reward(s): Ring of Contentment

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Wandering around Crucible, you will sooner or later come across Hirrus Clutumnus in a state of abject misery. He will ask you to meet him after dark at the sewer gate northeast of the statue of Sheogorath on his throne. (Your compass will lead you there). When you meet him, he will tell you his life is not worth living, and ask you to kill him. But you must do this unexpectedly and with no witnesses.

As a side note, this is somewhat similar to the quest when you become Champion of Cyrodiil in the Arena, when the former champion refuses to fight you and begs you to kill him. The difference is that in the Arena you have no option, because the gates are locked until the battle is concluded. Here you may have a moral dilemma, and so, if you prefer, you can just walk away from this quest, as it has no relevance to the main game.

Assuming you decide to proceed, go into sneak mode and follow Hirrus until you find a quiet spot on a bridge, where you can just shove him over the edge. Get his house key from his body and go to his home (compass again) to get your reward. This is the ironically named Ring of Contentment, which can be found in his jewel box on top of the wardrobe in his bedroom.